34762-17-9

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl 2-(bromomethyl)malonate is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and improving the efficacy of existing ones. Its unique structure allows for the creation of complex organic compounds that can target specific biological pathways.
Used in Agrochemical Industry:
In the agrochemical sector, Diethyl 2-(bromomethyl)malonate serves as a crucial component in the production of pesticides and other crop protection agents. Its incorporation enhances the effectiveness of these chemicals, ensuring better protection for crops and increased agricultural yields.
Used in Research and Development:
Diethyl 2-(bromomethyl)malonate is utilized in the research and development of new chemical processes and materials. Its versatility and reactivity make it an essential tool for scientists exploring innovative applications and pushing the boundaries of chemical synthesis.
Used in Fine Chemicals Production:
Diethyl2-(bromomethyl)malonate is also used as a building block in the production of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, flavors, and specialty chemicals. Its unique properties allow for the creation of high-quality products with specific characteristics.
It is important to handle Diethyl 2-(bromomethyl)malonate with care, as it is classified as hazardous. Proper safety measures and a controlled environment are necessary during its use to ensure the safety of personnel and the integrity of the process.

InChI:InChI=1/C8H13BrO4/c1-3-12-7(10)6(5-9)8(11)13-4-2/h6H,3-5H2,1-2H3

Synthetic route

diethyl ethoxymethylenemalonate (30379-04-5) → ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9)

Conditions	Yield
With hydrogen bromide In ethanol for 48h;	65%
With water; hydrogen bromide

diethyl methylenemalonate (3377-20-6) → ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9)

Conditions	Yield
With diethyl ether; hydrogen bromide

sodium diethylmalonate (996-82-7, 34727-00-9, 73177-21-6) → ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: water; hydrobromic acid View Scheme

2-aminopyridine (504-29-0) + ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) → C13H18N2O4

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at -20 - -15℃; for 8.5h; Solvent; Temperature; Reagent/catalyst;	91.7%

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + ethyl 3-hydroxyphenylacetate (22446-38-4) → C18H24O7 (1289544-57-5)

Conditions	Yield
Stage #1: ethyl 3-hydroxyphenylacetate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: ethyl 3-bromo-2-(ethoxycarbonyl)propionate In N,N-dimethyl-formamide at 110℃; Inert atmosphere;	65%

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + methylamine hydrochloride (593-51-1) → 2,2'-(2-methyl-2-aza-propanediyl)-di-malonic acid tetraethyl ester

Conditions	Yield
With ethanol; silver(l) oxide

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + potassium phtalimide (1074-82-4) → phthalimidomethyl-malonic acid diethyl ester (5101-83-7)

Conditions	Yield
With xylene

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) → diethyl 2-azido-2-methylmalonate (849114-26-7)

Conditions	Yield
With sodium azide; ethanol

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + triphenylphosphine (603-35-0) → (2,2-Bis-ethoxycarbonyl-ethyl)-triphenyl-phosphonium; bromide (34762-20-4)

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + <1>isoquinolyl-methyl lithium → (2-[1]isoquinolyl-ethyl)-malonic acid diethyl ester (101719-34-0)

Conditions	Yield
With diethyl ether

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + acetic acid (64-19-7) + zinc → methyl-propanedioic acid (516-05-2)

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) → bromo-phthalimidomethyl-malonic acid diethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: xylene 2: chloroform; bromine View Scheme

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + N-[(1R)-1-methyl-2-propen-1-yl]-2-pyridinesulfonamide (861848-44-4) → C17H24N2O6S

Conditions	Yield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 115℃; for 17h; Inert atmosphere; Large scale reaction;

ethyl 3-bromo-2-(ethoxycarbonyl)propionate (34762-17-9) + 1-benzyl-3-hydroxy-1H-indazole (2215-63-6) → diethyl 2-(((1-benzyl-1H-indazol-3-yl)oxy)methyl)malonate

Conditions	Yield
Stage #1: 1-benzyl-3-hydroxy-1H-indazole With potassium carbonate In 1,2-dimethoxyethane at 20℃; for 0.166667h; Stage #2: ethyl 3-bromo-2-(ethoxycarbonyl)propionate In 1,2-dimethoxyethane for 4h; Reflux;

Upstream product

• 3377-20-6 diethyl methylenemalonate 
• 30379-04-5 diethyl ethoxymethylenemalonate 
• 996-82-7 sodium diethylmalonate 

Downstream Products

• 34762-20-4 (2,2-Bis-ethoxycarbonyl-ethyl)-triphenyl-phosphonium; bromide 
• 516-05-2 methyl-propanedioic acid 
• 1289544-57-5 C₁₈H₂₄O₇ 

Relevant academic research and scientific papers

277. Structure and Chemistry of Malonylmethyl- and Succinyl-Radicals. The Search for Homolytic 1,2-Rearrangements

Malonylmethyl radical I and its thioester analogue II were generated by standard photolytic and thermolytic methods from perester and bromo precursors.The structures of I and II were examined by ESR spectroscopy and found to exist in preferred conformations.However, no indication for their rearrangement by 1,2-shift of either an ethoxycarboxyl or (ethylthio)carbonyl group to the corresponding succinyl radicals III and IV, respectively, was found at temperatures below -40 deg C.At higher temperatures of up to 140 deg C, the search for malonylmethyl -> succinyl rearrangement was examined by thorough-product analysis of the perester decomposition.There is evidence for the rearrangement of the radical I to III by photolysis and of the radical II to IV by thermolysis at 130 deg C in chlorobenzene to only a small extent.